Curiosity #11 - The Dark Forest of Leadership

🎤 Quotable quotes: “Gentlemen, believing in Rom-Communism is all about believing that everything's gonna work out in the end.” – Ted Lasso

📰 Let's start with this week's leadership musings by Marnie Stockman & Nick Coniglio

The Dark Forest of Leadership

If there’s one thing Ted Lasso teaches us (besides the importance of biscuits and hope), it’s that life is a story—and sometimes, you find yourself smack dab in the middle of your dark forest. You know the one: the part of the story where nothing’s going right, everything’s hard, and it feels like you’ve misplaced the map.

But here’s the kicker (pun intended):
"Fairytales do not start, nor do they end, in the dark forest. That’s something that only shows up smack dab in the middle of a story. But it will all work out."

Let’s pause for a moment because that’s a truth bomb wrapped in a warm blanket of optimism. Whether you’re leading a team, managing a project, or just trying to make it through your Tuesday, the dark forest isn’t the end of the story. It’s just the messy, necessary middle. (And trust us—every leader has been there. Some of us live there for a while.)

Ted goes on to say:
"It may not work out how you think it will, or how you hope it does, but believe me, it will all work out. Exactly as it's supposed to."

Ah, the old “let go of expectations” trick. Easier said than done, right? (We know—Marnie has tried letting go of expectations about Nick's mood on Mondays after a NY Jets game) But when you stop clinging to a rigid outcome, you make space for creativity, growth, and solutions that surprise you.

Leadership Takeaway: Making Peace with the Messy Middle

Here’s the thing about the dark forest: it’s where the good stuff happens (even if it doesn’t feel good at the time). You discover what you’re made of. You get scrappy. You learn to laugh at the absurdity of it all. Most importantly, you build resilience—and let’s be clear: resilience isn’t something you’re born with. It’s a muscle. And like any muscle, it gets stronger the more you use it.

So, what can you do when you or your team are slogging through the forest? Here are some ideas:

• Call it out (but keep it light): Sometimes, saying “Welp, we’re in the dark forest, folks!” makes it less scary.
• Tackle it step by step: Don’t worry about the whole forest—just focus on finding the next breadcrumb.
• Celebrate the tiny wins: Did you survive Monday? Boom. Win. Celebrate that.
• Practice resilience: Think of each challenge as a rep in your “resilience gym.” It’s not fun (burpees never are), but it’s how you grow stronger for the next big adventure.
• Remember: this too shall pass: Like Ted says, “It will all work out.” (And hey, even if it doesn’t go as planned, you’ll have a great story later.)

More leadership musings

🎁 Bonus: If you’re feeling stuck, go rewatch Season 2, Episode 5. (You know the one. Rom-Communism, Isaac rediscovering his mojo, Nate’s confidence journey, and a side of leadership lessons. It’s basically a playbook for believing.)

🍪 Biscuits with the Boss: What’s one “dark forest” moment you’ve overcome, and what’s a piece of advice you’d give to someone still finding their way out?

Sharing stories of resilience not only reminds us of our own strength but can also inspire and encourage others to keep going.

🏅Whistle. Whistle. If, like Roy Kent, you subscribe to the TL;DR; perspective... Roy might sum up this newlsetter up tightly with something like:

"Dark forest, my arse. It’s just life being life—messy, hard, and full of crap you’ve gotta deal with. So stop whining, get on with it, and come out swinging."

📚Beard’s collection: Recommended books and articles

📖 Holiday, Ryan and Hanselman, Stephen. The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living. Profile Trade, Main edition, 2016.

Holiday and Hanselman offer bite-sized daily meditations on resilience, discipline, and clarity that perfectly compliment the themes of navigating the dark forest and embracing life's challenges.

📖 Brown, Brené. Rising Strong: How the Ability to Reset Transforms the Way We Live, Parent, and Lead. Random House, 2016.

Brené dives into what happens when we face failure, heartbreak, or disappointment—and how the process of getting back up again is where true strength and transformation happen. A must-read for leaders navigating their messy middles.

📖 Frankl, Viktor E. Man's Search for Meaning. Beacon Press, 2006.

Written by a Holocaust survivor and psychiatrist, this profound book explores how finding meaning in suffering can help people endure the most challenging circumstances. It’s a testament to resilience and the power of belief.

🌎 This week in Here - There - Every F’ing where 

These leaders dished out some outstanding advice at our leadership breakfast at Northstar's Leadership Forum's event. I hope everyone went home with as many new ideas as I did!

Until next week—stay curious, stay resilient, and keep believing!

Marnie and Nick

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